Sodium Hydroxide → HCID 59361922, compound

HRID 61662Notes

Reaction equation

HRID 61662 reaction equation
[CH3:1][O:2][C:3]1[C:15]([O:16][CH2:17][CH2:18][O:19][CH3:20])=[CH:14][C:6]([C:7]([O:9]CCOC)=[O:8])=[C:5]([N+:21]([O-:23])=[O:22])[CH:4]=1.[OH-].[Na+]>CCO.O>[CH3:1][O:2][C:3]1[C:15]([O:16][CH2:17][CH2:18][O:19][CH3:20])=[CH:14][C:6]([C:7]([OH:9])=[O:8])=[C:5]([N+:21]([O-:23])=[O:22])[CH:4]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 59361944HCID 59361944, compound

Product 1

HCID 59361922HCID 59361922, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2-methoxyethyl 4-methoxy-5-(2-methoxyethoxy)-2-nitrobenzoate (5.0 g, 15.2 mmol) in EtOH (40 mL) was added 2N NaOH (40 mL, 76.0 mmol, 5 eq.). The mixture was stirred at RT for 12 h. The mixture was diluted with water (100 mL) and washed with CH2Cl2 (1×100 mL). The aqueous layer was acidified to pH=1 using 1N HCl (A solid began to precipitate, this was dissolved by the addition of EtOAc). The aqueous mixture was extracted with EtOAc (2×200 mL). The combined organics were washed with brine (1×100 mL), dried (Na2SO4), filtered and concentrated in vacuo to give 4-methoxy-5-(2-methoxyethoxy)-2-nitrobenzoic acid as an off white solid (3.55 g, 12.4 mmol, 86%). HPLC retention time 4.94 mins.

Workup

  1. washwashed with CH2Cl2 (1×100 mL)
  2. customto precipitate
  3. dissolutionthis was dissolved by the addition of EtOAc)
  4. extractionThe aqueous mixture was extracted with EtOAc (2×200 mL)
  5. washThe combined organics were washed with brine (1×100 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f64c083be2c44a3d87412dffeba1dbc8
Source dataset
uspto-grants-2016_09
Patent number
US09440961B2

Reaction notes

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